Asymmetric synthesis of β-amino cyclohexyl sulfonates, β-sultams and γ-sultones

Synthesis

Volumn , Issue 12, 2003, Pages 1856-1868

  Enders, Dieter ^a   Wallert, Stefan ^a   Runsink, Jan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Hydrazines; Michael addition; Sulfonates; sultams; sultones

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; HYDRAZINE;

LEWIS ACID;

SYNTHESIS (CHEMICAL);

1,2 THIAZETIDINE 1,1 DIOXIDE DERIVATIVE; BETA AMINOCYCLOHEXYL SULFONATE DERIVATIVE; GAMMA SULTONE DERIVATIVE; LEWIS ACID; OXIDE; SULFONIC ACID DERIVATIVE; SULTONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; STEREOISOMERISM;

EID: 0141742438     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41029     Document Type: Article

References (57)

1. Abbenante, G.; Hughes, R.; Prager, R. H. Aust. J. Chem. 1997, 50, 523.
2. Kobayashi, J.; Mikami, S.; Shigemori, H.; Takao, T.; Shimonoishi, Y.; Izuta, S.; Yoshida, S. Tetrahedron 1995, 38, 10487.
3. (a) Gennari, C.; Gude, M.; Potenza, D.; Piarulli, U. Chem. Eur. J. 1998, 4, 1924.
4. (b) Gude, M.; Piarulli, U.; Potenza, D.; Salom, B.; Gennari, C. Tetrahedron Lett. 1996, 37, 8589.
5. (c) Liskamp, R. M. J.; Moree, W. J.; van Gent, L. C.; van der Marel, G. A. Tetrahedron 1993, 49, 1133.
6. (d) Liskamp, R. M. J.; Moree, W. J.; van der Marel, G. A. J. Org. Chem. 1995, 60, 5157.
7. White, E. H.; Paik, S. Tetrahedron Lett. 1996, 37, 4663.
8. Liskamp, R. M. J.; Monnee, M. C. F.; Marline, M. F.; Brouwer, A. J. Tetrahedron Lett. 2000, 41, 7991.
9. Enders, D.; Wallert, S. Synlett 2002, 304.
10. (a) Otto, H. H.; Schwenkkraus, P. Tetrahedron Lett. 1982, 23, 5389.
11. (b) Cavagna, F.; Koller, W.; Linkies, A.; Rehling, H.; Reuschling, D. Angew. Chem., Int. Ed. Engl. 1982, 7, 548; Angew. Chem. 1982, 7, 549.
12. (b) Cavagna, F.; Koller, W.; Linkies, A.; Rehling, H.; Reuschling, D. Angew. Chem., Int. Ed. Engl. 1982, 7, 548; Angew. Chem. 1982, 7, 549.
13. (c) Müller, M.; Otto, H. H. Liebigs Ann. 1990, 171.
14. Baxter, N. J.; Rigoreau, L. J. M.; Laws, A. P.; Page, M. I. J. Am. Chem. Soc. 2000, 122, 3375.
15. Beardsell, M.; Hinchliffe, P. S.; Wood, J. M.; Wilmouth, R. C.; Schofield, C. J.; Page, M. I. Chem. Commun. 2001, 497.
16. (a) Iwama, T.; Kataoka, T.; Muraoka, O.; Tanabe, G. Tetrahedron 1998, 54, 5507.
17. (b) Kataoka, T.; Iwama, T.; Takagi, A. Tetrahedron Lett. 1996, 37, 2257.
18. (c) Iwama, T.; Ogawa, M.; Kataoka, T., Muraoka, O.; Tanabe, G. Tetrahedron 1998, 54, 8941.
19. Erdmann, H. Justus Liebigs Ann. Chem. 1888, 247, 306.
20. Fischer, R. F. Ind. Eng. Chem. 1964, 56, 41.
21. (a) Metz, P. J. Prakt. Chem. 1998, 340, 1.
22. (b) Buglass, A. J.; Tillet, J. G. The Chemistry of Sulfonic Acids, Esters and their Derivatives; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1991, Chap. 19.
23. (c) Roberts, D. W.; Williams, D. L. Tetrahedron 1987, 43, 1027.
24. Berre, A.; Etienne, A.; Dumaitre, B. Bull. Soc. Chim. Fr. 1970, 946.
25. (a) Meyle, E.; Keller, E.; Otto, H. H. Liebigs Ann. 1985, 802.
26. (b) Wilken, J.; Thorey, C.; Gröger, H.; Haase, D.; Saak, W.; Pohl, S.; Muzart, J.; Martens, J. Liebigs Ann./Recl. 1997, 2133.
27. (c) King, J. F.; Loosmore, S. M.; Aslam, M.; Lock, J. D.; McGarrity, M. J. J. Am. Chem. Soc. 1982, 104, 7108.
28. (d) Berre, A.; Delacroix, A.; Gressin, J. C.; Masson, J. C. Bull. Soc. Chim. Fr. 1976, 1845.
29. (e) Liskamp, R. M. J.; Ameijde, J. Tetrahedron Lett. 2000, 41, 1103.
30. (f) Makara, G. M.; Ma, Y. Tetrahedron Lett. 2001, 42, 4123.
31. (a) Enders, D. In Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: Orlando, 1984, 275.
32. (b) Enders, D.; Fey, P.; Kipphardt, H. Org Synth. 1987, 65, 173.
33. (c) Enders, D.; Fey, P.; Kipphardt, H. Org Synth. 1987, 65, 183.
34. (d) Review: Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
35. Martens, J.; Lübben, S. Liebigs Ann. 1990, 949.
36. Blanchette, M. A.; Choy, W., Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Skai, T. Tetrahedron Lett. 1984, 25, 2183.
37. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
38. Enders, D.; Müller, S.; Raabe, G. Angew. Chem. Int. Ed. 1999, 38, 195; Angew. Chem. 1999, 111, 212.
39. Enders, D.; Müller, S.; Raabe, G. Angew. Chem. Int. Ed. 1999, 38, 195; Angew. Chem. 1999, 111, 212.
40. Enders, D.; Lochtmann, R.; Meiers, M.; Müller, S. F.; Lazny, R. Synlett 1998, 1182.
41. (a) Schwenkkraus, P.; Merkle, S.; Otto, H. H. Liebigs Ann./Recl. 1997, 1261.
42. (b) Koller, W., Linkies, A.; Rehling, H.; Reuschling, D. Tetrahedron Lett. 1983, 24, 2131.
43. (c) Meyle, E.; Keller, E.; Otto, H. H. Liebigs Ann. 1985, 802.
44. (d) Schwenkkraus, P.; Otto, H. H. Liebigs Ann. 1994, 251.
45. (a) Grunder, E.; Leclerc, G. Synthesis 1989, 135.
46. (b) Szymonifka, M. J.; Heck, J. V. Tetrahedron Lett. 1989, 30, 2869.
47. Gordeev, M. F.; Gordon, E. M.; Patel, D. V. J. Org. Chem. 1997, 62, 8177.
48. Baldoli, C.; Del Buttero, P.; Perdicchia, D.; Pilati, T. Tetrahedron 1999, 55, 14089.
49. Wallert, S.; Enders, D. Tetrahedron Lett. 2002, 43, 5109.
50. Asao, N., Meguro, M.; Yamamoto, Y. Synlett 1994, 185.
51. (a) Metz, P.; Fleischer, M. Synlett 1993, 399.
52. (b) Metz, P.; Fleischer, M.; Fröhlich, R. Tetrahedron 1995, 51, 711.
53. Enders, D.; Vignola, N.; Harnying, W. Synlett 2002, 1727.
54. (a) Harding, K. E.; Tiner, T. H. Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I.; Semmelhack, M., Eds.; Pergamon: New York, 1991, 363.
55. (b) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
56. (c) Bartlett, P. A. Tetrahedron 1980, 36, 3.
57. (d) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Tetrahedron 1984, 40, 2317.